Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 24, Problem 24.25P
It is typically very difficult to do a substitution reaction on an
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It is typically very difficult to do a substitution reaction on an aromatic ring when the
leaving group is flanked by two other bulky substituents. Moreover, in Section 22.3, we
found that nucleophilic aromatic substitution requires strongly electron-withdrawing
groups on the benzene ring. However, Pd-catalyzed coupling allows entry into such
products. As examples, write the products of the following reactions and state which
coupling reaction is being utilized.
Ph
n-BugSn
Pd(0), PPhg
ÓTf
excess
Pd(PPH3)4, Cul, NE13
Substitutions on aromatic rings are generally carried out by electrophilic substitution, but for the synthesis of phenolic compounds and alkoxy benzene it is carried out by nucleophilic substitution, explain why this is so .
Ethane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below.CH3CH3+ Cl2→ CH3CH2Cl+ HClDescribe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish.
Chapter 24 Solutions
Organic Chemistry
Ch. 24.3 - Prob. 24.1PCh. 24.3 - Prob. 24.2PCh. 24.4 - Prob. 24.3PCh. 24.5 - Show how the following compound can be prepared...Ch. 24.5 - Prob. 24.5PCh. 24.5 - Prob. 24.6PCh. 24.6 - Prob. 24.7PCh. 24 - Prob. 24.8PCh. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Treatment of cyclohexene with iodobenzene under...Ch. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - The aryl diene undergoes sequential Heck reactions...Ch. 24 - Heck reactions take place with alkynes as well as...Ch. 24 - Prob. 24.16PCh. 24 - The following transformation involves a series of...Ch. 24 - Show the sequence of Heck reactions by which the...Ch. 24 - Prob. 24.19PCh. 24 - Write the steps that are critical in the following...Ch. 24 - Prob. 24.21PCh. 24 - Prob. 24.22PCh. 24 - Prob. 24.23PCh. 24 - Show how the following compound could be prepared...Ch. 24 - It is typically very difficult to do a...Ch. 24 - The compound eutypine is an antibacterial agent...Ch. 24 - Prob. 24.27PCh. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - Prob. 24.30PCh. 24 - Prob. 24.31PCh. 24 - Prob. 24.32PCh. 24 - Prob. 24.33PCh. 24 - The following transformation can be accomplished...Ch. 24 - Prob. 24.35PCh. 24 - Prob. 24.36PCh. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - E. J. Coreys 1964 total synthesis of...Ch. 24 - Prob. 24.40P
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- The Friedel-Crafts Alkylation of p-xylene n-propyl bromide can result in an isopropyl as well as n-propyl substitution. A) Write the chemical equation involved in this reaction. B) Which will be the major and minor product? What do you expect will be the ratio of n-propyl to isopropyl substitution for p-xylene?arrow_forwardEthane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below. CH3CH3 + Cl2 → CH3CH2Cl + HCl Describe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish. Would this reaction (question 34(c)) give a high yield of 1-chloroethanearrow_forwardEthane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below. CH3CH3 + Cl2 → CH3CH2Cl + HCl Describe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes placearrow_forward
- Ethane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below. CH3CH3 + Cl2 → CH3CH2Cl + HCl Describe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish.arrow_forwardUsing Friedel Crafts alkylation of benzene, a group of scientists discovered compound A, C3H3O, an optically inactive compound. They discovered that compound B, CsH;BrO, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C3H,B1NO3, is formed. While Friedel Crafts alkylation of compound A produces compound D. This compound D was oxidised to produce compound E, C9H§O3 as a major product. Compound F, C10H1002, was produced by Friedel Crafts acylation of compound A. This compound F reacts positively with alkaline iodine and 2,4- dinitrophenylhydrazine. However, it returns negative results for Tollens' and Benedict's tests. Identify the possible structural formulae compounds A to F and explain your answers.arrow_forward1) Discuss three methods that can be utilised to synthesise n – heptane in the laboratory.arrow_forward
- An electron-deficient carbon atom reacts with a nucleophile, symbolized as: Nu−. Define this ?arrow_forwardQuestion #19.arrow_forward(a) Draw the three isomers of benzenedicarboxylic acid.(b) The isomers have melting points of 210 °C, 343 °C, and 427 °C. Nitration of the isomers at all possible positions was once used to determine their structures. The isomer that melts at 210 °C gives two mononitro isomers. The isomer that melts at 343 °C gives three mononitro isomers. The isomer that melts at 427 °C gives only one mononitro isomer. Show which isomer has which melting point.arrow_forward
- Black powder (see introduction) was the propellant used in rifles and pistols during the 1860’s. Would it have been possible to use diphenylamine to detect gunshot residue on John Wilkes Booth after the assignation of President Lincoln? Why or Why not?arrow_forwardExplains the general concept of the manufacture of benzene by dealkylation of toluene with hydrogen.arrow_forwardThe major product formed when methylenecyclohexane is treated with NBS in dichloromethane is 1-(bromomethyl)cyclohexene. Account for the formation of this product.arrow_forward
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